Graphene-catalyzed transacetalization under acid-free conditions. Issue 41 (12th October 2016)

• Record Type: Journal Article
• Authors: Nongbe, Medy C.; Oger, Nicolas; Ekou, Tchirioua; Ekou, Lynda; Yao, Benjamin K.; Le Grognec, Erwan; Felpin, François-Xavier
• Is Part Of: Tetrahedron letters. Volume 57:Issue 41(2016)
• Page Start: 4637
• Page End: 4639
• Publication Date: 2016-10-12
• Subjects: Graphene -- Transacetalization -- Diol -- Heterogeneous catalysis -- Acid-free conditions; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.09.022
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 1, 2- and 1, 3-Diols are readily protected by graphene-catalyzed transacetalization. This is performed under Brønsted and Lewis acid-free conditions. The methodology features a simple protocol under solvent-free conditions. The quasi-stoichiometric acetal-to-diol molar ratio simplifies the work-up. The heterogeneous nature of graphene allows an easy removal of the catalyst. Abstract: 1, 2- and 1, 3-Diols are readily protected as cyclic acetals and ketals through a graphene-catalyzed transacetalization process. The methodology features an atom economic procedure since quasi-stoichiometric conditions have been developed. Unlike prior systems, the graphene-catalyzed transacetalization is performed under Brønsted and Lewis acid-free conditions and without solvent. Our method has been applied to several volatile compounds that are unsuitable for complex work-up and extensive purification steps. The very unusual catalytic properties of graphene for transacetalization reactions are ascribed to molecular charge transfer between graphene and substrates.